# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1517089'
_audit_update_record             
;
2016-11-14 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 Cl N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         433.87
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.5505(3)
_cell_length_b                   8.7111(4)
_cell_length_c                   9.9103(5)
_cell_angle_alpha                82.5366(18)
_cell_angle_beta                 73.6985(14)
_cell_angle_gamma                76.9181(18)
_cell_volume                     527.35(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5852
_cell_measurement_theta_min      4.6606
_cell_measurement_theta_max      68.1555
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226

_exptl_absorpt_coefficient_mu    1.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.83

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'BRUKER APEX-II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5780
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_theta_min         4.66
_diffrn_reflns_theta_max         68.13
_diffrn_reflns_theta_full        68.13
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2591
_reflns_number_gt                2571
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0768
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_refine_ls_number_reflns         2591
_refine_ls_number_parameters     281
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.0976P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 711 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.107(6)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6588(4) -0.2839(3) 0.3558(3) 0.0336(5) Uani d . . . 1 . .
C C2 0.6123(4) -0.0027(3) 0.3142(2) 0.0270(5) Uani d . . . 1 . .
C C3 0.5409(4) -0.0672(3) 0.1974(3) 0.0316(5) Uani d . . . 1 . .
H H3A 0.3827 -0.032 0.2086 0.038 Uiso calc U . R 1 . .
H H3B 0.6186 -0.03 0.1022 0.038 Uiso calc U . R 1 . .
C C4 0.5996(4) -0.2423(3) 0.2188(3) 0.0339(5) Uani d . . . 1 . .
C C5 0.4382(4) 0.1276(3) 0.3923(2) 0.0272(5) Uani d . . . 1 . .
C C6 0.2294(4) 0.0962(3) 0.4484(3) 0.0314(5) Uani d . . . 1 . .
H H6 0.202 -0.0027 0.4356 0.038 Uiso calc U . R 1 . .
C C7 0.0625(4) 0.2064(3) 0.5220(3) 0.0350(5) Uani d . . . 1 . .
H H7 -0.0777 0.1823 0.5605 0.042 Uiso calc U . R 1 . .
C C8 0.0998(4) 0.3522(3) 0.5396(3) 0.0395(6) Uani d . . . 1 . .
H H8 -0.0156 0.43 0.587 0.047 Uiso calc U . R 1 . .
C C9 0.3054(5) 0.3829(3) 0.4877(3) 0.0394(6) Uani d . . . 1 . .
H H9 0.3321 0.4818 0.5013 0.047 Uiso calc U . R 1 . .
C C10 0.4755(4) 0.2710(3) 0.4153(3) 0.0319(5) Uani d . . . 1 . .
H H10 0.6173 0.2933 0.3816 0.038 Uiso calc U . R 1 . .
C C11 0.8313(4) 0.0428(3) 0.2396(2) 0.0268(5) Uani d . . . 1 . .
C C12 0.9970(4) 0.2326(3) 0.0831(3) 0.0297(5) Uani d . . . 1 . .
C C13 1.0718(4) 0.2110(3) -0.0586(3) 0.0359(6) Uani d . . . 1 . .
H H13 1.0001 0.1571 -0.1029 0.043 Uiso calc U . R 1 . .
C C14 1.2534(4) 0.2690(4) -0.1358(3) 0.0402(6) Uani d . . . 1 . .
H H14 1.3071 0.2557 -0.234 0.048 Uiso calc U . R 1 . .
C C15 1.3555(4) 0.3460(3) -0.0695(3) 0.0372(6) Uani d . . . 1 . .
C C16 1.2800(5) 0.3673(4) 0.0719(3) 0.0400(6) Uani d . . . 1 . .
H H16 1.3528 0.4202 0.1164 0.048 Uiso calc U . R 1 . .
C C17 1.0973(4) 0.3114(3) 0.1493(3) 0.0368(6) Uani d . . . 1 . .
H H17 1.0416 0.3272 0.247 0.044 Uiso calc U . R 1 . .
C C18 0.7243(4) -0.1431(3) 0.5331(2) 0.0282(5) Uani d . . . 1 . .
C C19 0.9305(4) -0.2253(3) 0.5388(3) 0.0306(5) Uani d . . . 1 . .
H H19 1.022 -0.2809 0.4604 0.037 Uiso calc U . R 1 . .
C C20 1.0044(4) -0.2274(3) 0.6575(3) 0.0326(5) Uani d . . . 1 . .
H H20 1.1441 -0.2862 0.6611 0.039 Uiso calc U . R 1 . .
C C21 0.8727(4) -0.1430(3) 0.7713(3) 0.0334(5) Uani d . . . 1 . .
C C22 0.6661(5) -0.0614(4) 0.7661(3) 0.0416(6) Uani d . . . 1 . .
H H22 0.5754 -0.0039 0.8436 0.05 Uiso calc U . R 1 . .
C C23 0.5915(4) -0.0633(3) 0.6488(3) 0.0383(6) Uani d . . . 1 . .
H H23 0.4485 -0.0098 0.6475 0.046 Uiso calc U . R 1 . .
C C24 1.1199(5) -0.2353(5) 0.9145(3) 0.0519(8) Uani d . . . 1 . .
H H24A 1.1041 -0.3447 0.9157 0.078 Uiso calc U . R 1 . .
H H24B 1.1388 -0.2172 1.0054 0.078 Uiso calc U . R 1 . .
H H24C 1.247 -0.2161 0.8392 0.078 Uiso calc U . R 1 . .
C C25 0.6096(5) -0.3516(4) 0.1345(4) 0.0491(7) Uani d . . . 1 . .
H H25A 0.5764 -0.3213 0.0462 0.059 Uiso calc U . R 1 . .
H H25B 0.65 -0.4603 0.1623 0.059 Uiso calc U . R 1 . .
Cl Cl1 1.58264(12) 0.42075(10) -0.16815(9) 0.0612(3) Uani d . . . 1 . .
N N1 0.6509(3) -0.1450(2) 0.4101(2) 0.0286(4) Uani d . . . 1 . .
O O1 0.9309(3) -0.1306(2) 0.8904(2) 0.0423(5) Uani d . . . 1 . .
O O2 0.8059(3) 0.1810(2) 0.15975(19) 0.0349(4) Uani d . . . 1 . .
O O3 1.0039(3) -0.0377(2) 0.24144(19) 0.0356(4) Uani d . . . 1 . .
O O4 0.7021(4) -0.4151(2) 0.4114(2) 0.0475(5) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O4 . 1.212(3) ?
C1 N1 . 1.372(3) ?
C1 C4 . 1.493(4) ?
C2 N1 . 1.480(3) ?
C2 C5 . 1.528(3) ?
C2 C11 . 1.533(3) ?
C2 C3 . 1.570(3) ?
C3 C4 . 1.488(4) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C25 . 1.326(4) ?
C5 C10 . 1.384(3) ?
C5 C6 . 1.399(3) ?
C6 C7 . 1.381(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.388(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.374(4) ?
C8 H8 . 0.95 ?
C9 C10 . 1.396(4) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 O3 . 1.191(3) ?
C11 O2 . 1.356(3) ?
C12 C13 . 1.375(4) ?
C12 C17 . 1.377(4) ?
C12 O2 . 1.406(3) ?
C13 C14 . 1.384(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.376(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.372(4) ?
C15 Cl1 . 1.746(3) ?
C16 C17 . 1.382(4) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C23 . 1.389(4) ?
C18 C19 . 1.391(3) ?
C18 N1 . 1.434(3) ?
C19 C20 . 1.389(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.392(4) ?
C20 H20 . 0.95 ?
C21 O1 . 1.362(3) ?
C21 C22 . 1.391(4) ?
C22 C23 . 1.385(4) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?
C24 O1 . 1.421(4) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 H25A . 0.95 ?
C25 H25B . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 C1 N1 . . 125.6(2) ?
O4 C1 C4 . . 127.1(2) ?
N1 C1 C4 . . 107.3(2) ?
N1 C2 C5 . . 110.97(18) ?
N1 C2 C11 . . 108.29(18) ?
C5 C2 C11 . . 115.62(19) ?
N1 C2 C3 . . 102.72(18) ?
C5 C2 C3 . . 112.91(18) ?
C11 C2 C3 . . 105.39(18) ?
C4 C3 C2 . . 105.03(19) ?
C4 C3 H3A . . 110.7 ?
C2 C3 H3A . . 110.7 ?
C4 C3 H3B . . 110.7 ?
C2 C3 H3B . . 110.7 ?
H3A C3 H3B . . 108.8 ?
C25 C4 C3 . . 129.2(3) ?
C25 C4 C1 . . 121.9(3) ?
C3 C4 C1 . . 108.8(2) ?
C10 C5 C6 . . 118.3(2) ?
C10 C5 C2 . . 124.4(2) ?
C6 C5 C2 . . 117.2(2) ?
C7 C6 C5 . . 121.3(2) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 C8 . . 119.9(2) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 119.3(2) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C8 C9 C10 . . 121.0(3) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C5 C10 C9 . . 120.2(2) ?
C5 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
O3 C11 O2 . . 123.4(2) ?
O3 C11 C2 . . 124.9(2) ?
O2 C11 C2 . . 111.41(18) ?
C13 C12 C17 . . 121.6(2) ?
C13 C12 O2 . . 118.8(2) ?
C17 C12 O2 . . 119.5(2) ?
C12 C13 C14 . . 118.9(2) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C15 C14 C13 . . 119.6(2) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C16 C15 C14 . . 121.2(3) ?
C16 C15 Cl1 . . 119.5(2) ?
C14 C15 Cl1 . . 119.3(2) ?
C15 C16 C17 . . 119.5(3) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C12 C17 C16 . . 119.2(2) ?
C12 C17 H17 . . 120.4 ?
C16 C17 H17 . . 120.4 ?
C23 C18 C19 . . 119.0(2) ?
C23 C18 N1 . . 121.3(2) ?
C19 C18 N1 . . 119.7(2) ?
C20 C19 C18 . . 120.9(2) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C19 C20 C21 . . 119.7(2) ?
C19 C20 H20 . . 120.2 ?
C21 C20 H20 . . 120.2 ?
O1 C21 C22 . . 115.6(2) ?
O1 C21 C20 . . 125.0(2) ?
C22 C21 C20 . . 119.4(2) ?
C23 C22 C21 . . 120.5(2) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C22 C23 C18 . . 120.4(2) ?
C22 C23 H23 . . 119.8 ?
C18 C23 H23 . . 119.8 ?
O1 C24 H24A . . 109.5 ?
O1 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
O1 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C4 C25 H25A . . 120.0 ?
C4 C25 H25B . . 120.0 ?
H25A C25 H25B . . 120.0 ?
C1 N1 C18 . . 121.6(2) ?
C1 N1 C2 . . 114.2(2) ?
C18 N1 C2 . . 122.68(19) ?
C21 O1 C24 . . 117.9(2) ?
C11 O2 C12 . . 116.49(17) ?

